US9994678B2 - Process for the continuous preparation of an aliphatic or partially aromatic polyamide - Google Patents

Process for the continuous preparation of an aliphatic or partially aromatic polyamide Download PDF

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US9994678B2
US9994678B2 US14/896,945 US201414896945A US9994678B2 US 9994678 B2 US9994678 B2 US 9994678B2 US 201414896945 A US201414896945 A US 201414896945A US 9994678 B2 US9994678 B2 US 9994678B2
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process according
zone
polyamide
oligomerization
temperature
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US20160145390A1 (en
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Christian Schmidt
Joachim Clauss
Axel Wilms
Volker Rauschenberger
Gad Kory
Stefan Schwiegk
Arnold Schneller
Achim Stammer
Frank Niedermaier
Bernd Hackel
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BASF SE
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BASF SE
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Assigned to BASF SE reassignment BASF SE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SCHWIEGK, STEFAN, SCHNELLER, ARNOLD, HACKEL, Bernd, NIEDERMAIER, Frank, STAMMER, ACHIM, KORY, GAD, WILMS, AXEL, RAUSCHENBERGER, VOLKER, CLAUSS, JOACHIM, SCHMIDT, CHRISTIAN
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/28—Preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids

Definitions

  • a further important field of use of the HTPAs is in high-temperature automotive applications. Important properties here are good heat aging resistance, and high strength and toughness and weld seam strength of the polymers used. Amorphous HTPAs or those having very low crystalline contents are transparent and are especially suitable for applications where transparency is advantageous. Semicrystalline HTPAs are generally notable for long-term stability at high ambient temperature and are suitable, for example, for applications in the engine bay area.
  • the oligomer formed is converted by dewatering to the solid phase and subjected to what is called a solid state polymerization (SSP).
  • SSP solid state polymerization
  • water is removed in a controlled manner and the temperature is increased to convert the aqueous solution to the melt for further polycondensation.
  • the polymerization in the melt in particular is not unproblematic, since unwanted side reactions also take place at the high temperatures required, and these can adversely affect the product quality.
  • a polymer having a number-average molecular weight of 13 000 to 22 000 g/mol is generally obtained.
  • a postpolymerization may then follow if required.
  • DE 4329676 A1 describes a process for continuous polycondensation of high molecular weight, especially amorphous, semiaromatic copolyamides, wherein a precondensate is first prepared from an aqueous reaction mixture while heating and at pressure at least 15 bar, then the temperature and pressure are increased to prepare a prepolymer and ultimately the copolyamide through condensation in a vented extruder. In the course of this, the water content is reduced as early as in the precondensation stage, and at the end of the precondensation is about 5 to 40% by weight.
  • the prepolymer is then prepared at 220 to 350° C. and a pressure of at least 20 bar.
  • the postpolymerization is then performed in a twin-screw extruder with venting zones.
  • the invention firstly provides a process for continuously preparing an aliphatic or semiaromatic polyamide, in which
  • the invention further provides for the use of an aliphatic polyamide obtainable by a process as defined above and hereinafter for production of films, monofilaments, fibers, yarns or textile fabrics.
  • the copolyamide may also comprise small amounts of other repeat units which may result from degradation reactions or side reactions of the monomers, for example of the diamines.
  • C 1 -C 4 -alkyl comprises unsubstituted straight-chain and branched C 1 -C 4 -alkyl groups.
  • Examples of C 1 -C 4 -alkyl groups are especially methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl(1,1-dimethylethyl).
  • step a) of the process according to the invention an aqueous composition comprising at least one component suitable for polyamide formation is provided.
  • the aromatic dicarboxylic acid A) used is terephthalic acid, isophthalic acid or a mixture of terephthalic acid and isophthalic acid.
  • the semiaromatic polyamides prepared by the process according to the invention have a proportion of aromatic dicarboxylic acids among all the dicarboxylic acids of at least 50 mol %, more preferably of 70 mol % to 100 mol %.
  • the semiaromatic polyamides prepared by the process according to the invention (and the prepolymers provided in step a)) have a proportion of terephthalic acid or isophthalic acid or a mixture of terephthalic acid and isophthalic acid, based on all the dicarboxylic acids, of at least 50 mol %, preferably of 70 mol % to 100 mol %.
  • the semiaromatic polyamides comprise exclusively bis(4-aminocyclohexyl)methane as the copolymerized diamine D).
  • acetic acid propionic acid, n-, iso- or tert-butyric acid, valeric acid, trimethylacetic acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, palmitic acid, stearic acid, pivalic acid, cyclohexanecarboxylic acid, benzoic acid, methylbenzoic acids, ⁇ -naphthalenecarboxylic acid, ⁇ -naphthalenecarboxylic acid, phenylacetic acid, oleic acid, ricinoleic acid, linoleic acid, linolenic acid, erucic acid, fatty acids from soya, linseeds, castor oil plants and sunflowers, acrylic acid, methacrylic acid, Versatic® acids, Koch® acids and mixtures thereof.
  • the monocarboxylic acid E) is selected from acetic acid, propionic acid, benzoic acid and mixtures thereof.
  • Suitable compounds K) are additionally 4-[(Z)—N-(6-aminohexyl)-C-hydroxycarbonimidoyl]benzoic acid, 3-[(Z)—N-(6-aminohexyl)-C-hydroxycarbonimidoyl]benzoic acid, (6Z)-6-(6-aminohexylimino)-6-hydroxyhexanecarboxylic acid, 4-[(Z)—N-[(5-amino-1,3,3-trimethylcyclohexyl)methyl]-C-hydroxycarbonimidoyl]benzoic acid, 3-[(Z)—N-[(5-amino-1,3,3-trimethylcyclohexyl)methyl]-C-hydroxycarbonimidoyl]benzoic acid, 4-[(Z)—N-[3-(aminomethyl)-3,5,5-trimethylcyclohexyl]-C-hydroxycarbonimidoyl]benzoic acid, 3-[(Z)
  • tin compounds suitable as catalysts include tin(II) oxide, tin(II) hydroxide, tin(II) salts of mono- or polybasic carboxylic acids, e.g. tin(II) dibenzoate, tin(II) di(2-ethylhexanoate), tin(II) oxalate, dibutyltin oxide, butyltin acid (C 4 H 9 —SnOOH), dibutyltin dilaurate, etc.
  • Suitable lead compounds are, for example, lead(II) oxide, lead(II) hydroxide, lead(II) acetate, basic lead(II) acetate, lead(II) carbonate, etc.
  • the tubular reactors or tube bundle reactors used for the reaction in step b) are not backmixed. Thus, they preferably do not have any backmixing internals.
  • the temperature and pressure values used for the oligomerization are selected such that essentially no proportions of the component used for polyamide formation are present in the gas phase.
  • the output from the oligomerization zone is fed into a flash zone E1) and subjected to an expansion to obtain a water-containing gas phase and a liquid phase comprising the polyamide oligomers, and at least a portion of the water-containing gas phase is removed.
  • the absolute pressure in the flash zone E1) in step c) is within a range from 10 to 50 bar, preferably from 20 to 35 bar.
  • the pressure can be reduced before the rapid heating in step d).
  • This reduction in the pressure can be performed with an apparatus customary therefor. This includes the use of at least one pressure-reducing valve.
  • the pressure of the output from the oligomerization zone is reduced to an absolute pressure at least 5 bar, preferably at least 10 bar, below the pressure in the oligomerization zone.
  • the reduction in the pressure prior to the rapid heating in step d) is effected specifically with the proviso that no solid phase comprising polyamide oligomers is obtained.
  • the residence time in the coiled tube evaporator can be controlled via the flowrate and especially via the geometric dimensions, for example the tube length and/or internal tube diameter, of the coiled tube evaporator. More preferably, according to the desired mode of operation, it is possible to decompress a composition in a coiled tube evaporator to an absolute pressure in the region of less than 4 bar.
  • the flash zone E2) comprises an unstirred or stirred flash tank or consists of an unstirred or stirred flash tank.
  • the flash zone E2) may comprise one or more flash tanks.
  • Suitable flash tanks generally comprise a pressure-resistant closed vessel, a feed apparatus for the heated polyamide composition from step d), a pressure-reducing apparatus, a withdrawal apparatus for the water-containing gas phase and a withdrawal apparatus for the polyamides.
  • Suitable flash tanks are, for example, unstirred or stirred tanks, conical tanks, etc.
  • the temperature in the flash zone E2) in step e) is above the melting temperature Tm 2 of the aliphatic or semiaromatic polyamide.
  • the temperature in the flash zone E2) in step e) is at least 5° C., preferably at least 10° C., above the melting temperature Tm 2 of the aliphatic or semiaromatic polyamide.
  • the temperature in the flash zone E2) in step e) is at least 300° C., more preferably at least 310° C.
  • the temperature in the flash zone E2) is selected here as a function of the melting temperature of the polymer.
  • Useful filler materials include organic or inorganic fillers and reinforcers. For example, it is possible to use inorganic fillers, such as kaolin, chalk, wollastonite, talc, calcium carbonate, silicates, titanium dioxide, zinc oxide, graphite, glass particles, e.g.
  • the inventive molding compositions comprise preferably 0.01 to 3% by weight, more preferably 0.02 to 2% by weight and especially 0.1 to 1.5% by weight of at least one heat stabilizer.
  • the amount of these stabilizers is preferably 0.1 to 1.5% by weight, more preferably from 0.2 to 1% by weight, based on the sum of components A) to C).
  • Preferred halogen-free flame retardants are red phosphorus, phosphinic or diphosphinic salts and/or nitrogen-containing flame retardants such as melamine, melamine cyanurate, melamine sulfate, melamine borate, melamine oxalate, melamine phosphate (primary, secondary) or secondary melamine pyrophosphate, neopentyl glycol boric acid melamine, guanidine and derivatives thereof known to those skilled in the art, and also polymeric melamine phosphate (CAS No.: 56386-64-2 or 218768-84-4, and also EP 1095030), ammonium polyphosphate, trishydroxyethyl isocyanurate (optionally also ammonium polyphosphate in a mixture with trishydroxyethyl isocyanurate) (EP584567).
  • nitrogen-containing flame retardants such as melamine, melamine cyanurate, melamine sulfate, melamine bo
  • the inventive semiaromatic polyamides are advantageously suitable for use for production of moldings for electrical and electronic components and for high-temperature automotive applications.
  • the inventive semiaromatic polyamides are additionally specifically suitable for use in soldering operations under lead-free conditions (lead free soldering), for production of plug connectors, microswitches, microbuttons and semiconductor components, especially reflector housings of light-emitting diodes (LEDs).
  • LEDs light-emitting diodes
  • polyamides with improved flow for the kitchen and household sector are for production of components for kitchen machines, for example fryers, smoothing irons, knobs, and also applications in the garden and leisure sector, for example components for irrigation systems or garden equipment and door handles.
  • the output from the oligomerization was subjected to rapid heating in a heat exchanger operated at 35 barg and 320° C. and the pressure was reduced by means of a pressure-reducing valve.
  • the feedstocks were oligomerized at internal temperature 230° C. for 1 hour and then at internal temperature 240° C. for a further 30 minutes, in each case at a pressure of 40 barg. This was followed by rapid heating to 320° C. at 35 barg. The output from the heat exchanger was expanded to 7.5 barg at 320° C. and the water-containing gas phase formed was removed. The polyamide composition remained at these temperature and pressure values for about another 7 minutes for postpolymerization in the separator and was then discharged for analysis.
  • TPA terephthalic acid
  • the feedstocks were oligomerized at internal temperature 200° C. for 1 hour and then at internal temperature 240° C. for a further 30 minutes, in each case at a pressure of 45 barg. This was followed by rapid heating to 320° C. at 45 barg. The output from the heat exchanger was expanded to 6 barg at 320° C. and the water-containing gas phase formed was removed. The polyamide composition remained at these temperature and pressure values for about another 7 minutes for postpolymerization in the separator and was then discharged for analysis.
  • TPA terephthalic acid
  • the feedstocks were oligomerized at internal temperature 240° C. for 1 hour, at a pressure of 40 barg. This was followed by expansion at 242° C. and 31 barg for about 25 min and removal of the water-containing gas phase formed. This was followed by rapid heating to 320° C. at 30 barg. The output from the heat exchanger was expanded to 7 barg at 320° C. and the water-containing gas phase formed was removed. The polyamide composition remained at these temperature and pressure values for about another 8 minutes for postpolymerization in the separator and was then discharged for analysis.
  • TPA terephthalic acid
  • DSC Differential scanning calorimetry

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyamides (AREA)
  • Heat-Exchange Devices With Radiators And Conduit Assemblies (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Artificial Filaments (AREA)
US14/896,945 2013-06-12 2014-06-11 Process for the continuous preparation of an aliphatic or partially aromatic polyamide Active US9994678B2 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
EP13171651 2013-06-12
EP13171651 2013-06-12
EP13171651.6 2013-06-12
EP14162299 2014-03-28
EP14162299 2014-03-28
EP14162299.3 2014-03-28
PCT/EP2014/062105 WO2014198759A1 (de) 2013-06-12 2014-06-11 Verfahren zur kontinuierlichen herstellung eines aliphatischen oder teilaromatischen polyamids

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EP (1) EP3008110A1 (ja)
JP (1) JP6521952B2 (ja)
KR (1) KR102234828B1 (ja)
CN (1) CN105452334B (ja)
CA (1) CA2914510C (ja)
IL (1) IL242727B (ja)
MX (1) MX368538B (ja)
MY (1) MY186513A (ja)
SG (1) SG11201510168XA (ja)
WO (1) WO2014198759A1 (ja)

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US10889689B2 (en) 2016-03-21 2021-01-12 Basf Se Desalination of polyaryl ethers by means of melt extraction
US11701864B2 (en) 2017-10-27 2023-07-18 Mitsui Chemicals, Inc. Metal/resin composite structure and manufacturing method of metal/resin composite structure

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PL3390380T3 (pl) 2015-12-18 2020-09-21 Basf Se Odzyskiwanie energii w sposobie wytwarzania 1,3,5-trioksanu
EP3587472A4 (en) 2017-02-21 2020-04-01 Mitsubishi Gas Chemical Company, Inc. AMORPHOUS POLYAMIDE RESIN AND MOLDED ARTICLE
WO2019067517A1 (en) * 2017-09-28 2019-04-04 E. I. Du Pont De Nemours And Company POLYMERIZATION PROCESS
PL240713B1 (pl) * 2017-12-07 2022-05-23 Grupa Azoty Spolka Akcyjna Sposób otrzymywania kompozytów poliftalamidów z nanonapełniaczem krzemionkowym
EP3502165A1 (en) 2017-12-22 2019-06-26 Rhodia Operations Process for preparing a copolyamide without encrustation in the autoclave
SG11202011412UA (en) 2018-05-31 2020-12-30 Dow Global Technologies Llc Method and system for polymer production
CN108654549B (zh) * 2018-06-14 2020-03-20 吴贵岚 一种油酸酰胺连续化合成装置及其使用方法
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CN112779622A (zh) * 2019-11-07 2021-05-11 上海凯赛生物技术股份有限公司 一种聚酰胺56工业丝及其制备方法和应用
CN113861410B (zh) * 2021-10-28 2024-04-05 湖南世博瑞高分子新材料有限公司 一种pa6树脂连续聚合工艺
CN114316255B (zh) * 2022-01-21 2024-04-19 湖南世博瑞高分子新材料有限公司 一种耐高温尼龙连续熔融聚合方法

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